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Getting More Strategic

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Strategy – how to be strategic, and how to be seen as strategic – is one of my ongoing obsessions. Years ago, I read Good Strategy/Bad Strategy, and it’s guided my thinking ever since.

One of the things that book helps clarify is that being strategic and being seen as strategic can work against each other – good strategy is obvious, and usually it is executed on more than it’s talked about. An ongoing frustration for other under indexed people in tech I talk to, as we build products and organizations without drama, whilst being told we’re just “not strategic” enough. The strategy required to sidestep problems that never happen or that creates optionality to quickly resolve is somehow invisible.

But I think as we rise up the org chart, strategy is the job. Strategy defines your job, and evolves it to meet the organizational need. Not just one strategy, but multiple strategies that need to fit together and be coherent.

Your product strategy. Your technical strategy. Your team strategy. Your you-as-a-leader-but-also-a-human-being strategy.

As we find our groove in the resource constrained era we are in currently as opposed to the everything strategy of ZIRP (zero interest rates), by definition we need to make more harder choices, and strategy is how we know what those choices are, and when and how to make them.

This is the first rule of strategy: strategy is contextual. A crucial insight, because often when leaders fail, it’s because they tried to apply a strategy that worked in one context, to a different one, without considering the difference.

This is true when you change companies, and I think the reason why there is such a high failure rate for executive hires*. Ones I’ve watched fail came in with a playbook, usually including the org chart they wanted, and expended all the goodwill and capital in pursuit of that goal, whilst achieving very little.

It’s also the case that when the market changes, our strategy must change. One of the core features of ZIRP-era engineering leadership was hiring for the sake of it, and number of people as a proxy for many things it maybe (probably) shouldn’t have been. One of the biggest shifts has been the layoffs and the mantra of “doing more with less”. Regardless of personal feelings on this topic and what is actually realistic, it is apparent that hard choices and discipline are a key feature of the post-ZIRP era.

We could talk about these strategies – product, technical, team, you, like some balanced stool. But realistically, I think it’s more like the image above. The product strategy is a storm (especially pre-product market fit). The technical strategy is a half built shelter (you’ll get to it properly once you have product market fit). The team strategy is an umbrella (the most flexible and controllable). And the you as a human strategy is nowhere to be found.

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